Tert-butylthiol
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| Names | |
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Preferred IUPAC name
2-Methylpropane-2-thiol
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| Other names
t-BuSH
2-Methylpropane-2-thiol 2-Methyl-2-propanethiol tert-Butyl mercaptan |
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| Identifiers | |
75-66-1 
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| 3D model (Jmol) | Interactive image |
| Abbreviations | TBM |
| ChemSpider |
6147
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| ECHA InfoCard | 100.000.810 |
| PubChem | 6387 |
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| Properties | |
| C4H10S | |
| Molar mass | 90.18 g·mol−1 |
| Appearance | Colorless, clear liquid |
| Density | 0.8 g/mL |
| Melting point | −0.50 °C (31.10 °F; 272.65 K) |
| Boiling point | 62 to 65 °C (144 to 149 °F; 335 to 338 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
tert-Butylthiol, also known as 2-methylpropane-2-thiol, 2-methyl-2-propanethiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol is used as an odorant for natural gas, which is otherwise odorless. It may also have been used as a flavoring agent.
At least one publication has listed tert-butylthiol as a very minor component of cooked potatoes, but because the tert-butyl moiety is very rare in natural products, other sources doubt the existence of natural sources of the compound. The compound was first prepared in 1890 by Leonard Dobbin by the reaction of zinc sulfide and t-butyl chloride.
The compound was later prepared in 1932 by the reaction of the Grignard reagent, t-BuMgCl, with sulfur to give the corresponding thiolate, followed by hydrolysis. This preparation is shown below:
It is currently prepared industrially by the reaction of isobutylene with hydrogen sulfide over a clay (silica alumina) catalyst.
tert-Butylthiol can react with metal alkoxides and acyl chlorides to form thiol esters, as shown in the equation:
In the reaction above, thallium(I) ethoxide converts to thallium(I) t-butylthiolate. In the presence of diethyl ether, thallium(I) t-butylthiolate reacts with acyl chlorides to give the corresponding tert-butyl thioesters. Like other thioesters, it reverts to tert-butylthiol by hydrolysis.
Lithium 2-methylpropane-2-thiolate can be prepared by treatment of tert-butylthiol with lithium hydride in an aprotic solvent such as hexamethylphosphoramide (HMPA). The resulting thiolate salt is a useful demethylating reagent. For example, treatment with 7-methylguanosine gives guanosine. Other N-methylated nucleosides in tRNA are not demethylated by this reagent.
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